I'm getting back into dating with something I don't know when to mention: I'm 30, I've dated a little, and I've never had sex or been in a serious relationship. If things go well with a man, when does that become something he should know?
There isn't a religious explanation or a moral position behind it. It simply hasn't happened. That sounds straightforward until I imagine saying it to someone who may have assumed a completely different history. At my age, I feel as though experience comes presumed, and I'm the one who would have to interrupt that assumption.
I'm not especially ashamed of being inexperienced. Still, being comfortable with a fact about myself and telling it to a man I want to like me are different things. I worry that he could find it off-putting. I also worry about not being good enough for him, which makes a conversation about my past feel uncomfortably close to asking whether I'll disappoint him in the future.
Those worries aren't quite the same. A man could be perfectly accepting of my history and I could still feel nervous about having sex for the first time. Or he could care about the inexperience itself. Until there's an actual conversation, I can't know which concern would matter, or whether either would matter to him at all. So far, these are possibilities I'm turning over, not reactions I've received.
Some friends think I should just go with it. Their view is that men won't necessarily be able to tell, and I could spare myself the awkward conversation. I can understand the appeal: I could get to know someone without making my lack of experience the most memorable thing about me. Dating already means discovering whether two people like each other. I don't particularly want to arrive with an explanation prepared.
But their suggestion leaves me wondering about afterward. If I said nothing and he later found out, would he feel that I'd kept something important from him? I don't know whether he'd see it as an ordinary private detail or something he would have wanted to understand before we had sex. My friends' confidence that he wouldn't notice doesn't answer that part.
Timing changes the feeling of telling him, too. Mentioning it very early could give a hypothetical future together more weight than it has earned. Waiting until sex is likely could make an already vulnerable moment feel more exposed. I want enough familiarity for the conversation to feel personal, without feeling that I've let an assumption settle between us.
And being new to a serious relationship is its own piece of this. Sex is the obvious disclosure, but it isn't the only experience I haven't had. I would also be discovering what it feels like to build that kind of relationship with someone. I don't want the whole prospect reduced to one first time.
For now, I'm back at the beginning of dating, with no particular man's response to weigh. My friends say I could skip the awkwardness. I keep thinking about the moment afterward, when he might learn something about me he thought he already knew.
